4-Toluenesulfonyl chloride → HCID 13313521, compound

HRID 1981333Notes

Reaction equation

HRID 1981333 reaction equation
[Cl:1][C:2]1([Cl:9])[C:4]([CH3:6])([CH3:5])[CH:3]1[CH2:7][OH:8].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([O:8][CH2:7][CH:3]2[C:4]([CH3:6])([CH3:5])[C:2]2([Cl:9])[Cl:1])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12604182(2,2-Dichloro-3,3-dimethylcyclopropyl)methanol

Product 1

HCID 13313521HCID 13313521, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 33.8 g of 2,2-dichloro-3,3-dimethylcyclopropane methanol in 200 ml of pyridine was cooled to 0° C., and 38.2 g of p-toluenesulfonyl chloride was added portionwise. The reaction mixture was left to stand for 12 hours in a refrigerator (0° C.), and then poured into 1 liter of ice water. The crystals precipitated were collected by filtration, washed with water, dried in the air, and washed with hexane to give 62 g of 2,2-dichloro-3,3-dimethylcyclopropylmethyl p-toluenesulfonate, the desired compound shown above. The melting point of the product was 96.5° to 97.5° C.

Workup

  1. waitThe reaction mixture was left
  2. customThe crystals precipitated
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried in the air
  6. washwashed with hexane

Sources & evidence

ORD record
ord-a7beeba834054c92a6f8a1a4b53a7d3e
Source dataset
uspto-grants-1985_04
Patent number
US04514418

Reaction notes

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